Triethylene glycol monomethyl ether → m-PEG3-succinimidyl carbonate

HRID 513877Notes

Reaction equation

HRID 513877 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10]O.C1C(=O)N([O:19][C:20]([O:22][N:23]2[C:28](=[O:29])[CH2:27][CH2:26][C:24]2=[O:25])=[O:21])C(=O)C1.C(N(CC)CC)C.C(OCC)(=O)C>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:19][C:20](=[O:21])[O:22][N:23]1[C:24](=[O:25])[CH2:26][CH2:27][C:28]1=[O:29]

Participants

6

Reactant 4

HCID 8178Triethylene glycol monomethyl etherHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676246Di(succinimido) carbonate

Product 1

HCID 51340961m-PEG3-succinimidyl carbonateYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylene glycol monomethyl ether (1.0 g, 6.1 mmol) and N,N′-disuccinimidyl carbonate (1.87 g, 7.3 mmol) were dissolved in acetonitrile (10 mL). Then triethylamine (1.3 mL, 9.15 mmol) was added and the reaction stirred overnight at room temperature. Crude reaction was evaporated to dryness, dissolved in sat. NaHCO3 (50 mL), washed ethyl acetate (2×50 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate) afforded 1 a clear oil (0.367 g, 20% yield).

Workup

  1. customCrude reaction
  2. customwas evaporated to dryness
  3. dissolutiondissolved in sat. NaHCO3 (50 mL)
  4. washwashed ethyl acetate (2×50 mL), dried MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-51f5828fe79e4d2e82030a821233f723
Source dataset
uspto-grants-2015_08
Patent number
US09102758B2

Reaction notes

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